Branch-Selective Alkene Hydroarylation by Cooperative Destabilization: Iridium-Catalyzed ortho-Alkylation of Acetanilides

被引:82
作者
Crisenza, Giacomo E. M. [1 ]
Sokolova, Olga O. [1 ]
Bower, John F. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
acetanilides; branch selectivity; hydroarylation; iridium; phosphine ligands; C-H ACTIVATION; REDUCTIVE ELIMINATION; COUPLING REACTIONS; BOND FORMATION; COMPLEXES; FUNCTIONALIZATION; ARYLATION; INDOLE; ALKENYLATION; STABILITY;
D O I
10.1002/anie.201506581
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iridium(I) catalyst system, modified with the wide-bite-angle and electron-deficient bisphosphine d(F)ppb (1,4-bis(di(pentafluorophenyl)phosphino)butane) promotes highly branch-selective hydroarylation reactions between diverse acetanilides and aryl-or alkyl-substituted alkenes. This provides direct and ortho-selective access to synthetically challenging anilines, and addresses long-standing issues associated with related Friedel-Crafts alkylations.
引用
收藏
页码:14866 / 14870
页数:5
相关论文
共 63 条
[51]   A Meta-Selective Copper-Catalyzed C-H Bond Arylation [J].
Phipps, Robert J. ;
Gaunt, Matthew J. .
SCIENCE, 2009, 323 (5921) :1593-1597
[52]   Chan-Lam coupling reactions: synthesis of heterocycles [J].
Rao, Kodepelly Sanjeeva ;
Wu, Tian-Shung .
TETRAHEDRON, 2012, 68 (38) :7735-7754
[53]  
Rappoport Z., 2007, MACROMOL RAPID COMM, V29, P280
[54]   Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects [J].
Ritleng, V ;
Sirlin, C ;
Pfeffer, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1731-1769
[55]   Removable Directing Groups in Organic Synthesis and Catalysis [J].
Rousseau, Geraldine ;
Breit, Bernhard .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) :2450-2494
[56]   De Novo Synthesis of Multisubstituted Aryl Amines Using Alkene Cross Metathesis [J].
Tatton, Matthew R. ;
Simpson, Iain ;
Donohoe, Timothy J. .
ORGANIC LETTERS, 2014, 16 (07) :1920-1923
[57]   C-H nitrogenation and oxygenation by ruthenium catalysis [J].
Thirunavukkarasu, Vedhagiri S. ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2014, 50 (01) :29-39
[58]   Direct functionalization of unactivated C-H bonds catalyzed by group 3-5 metal alkyl complexes [J].
Tsurugi, Hayato ;
Yamamoto, Koji ;
Nagae, Haruki ;
Kaneko, Hiroshi ;
Mashima, Kazushi .
DALTON TRANSACTIONS, 2014, 43 (06) :2331-2343
[59]   N-H activation vs. C-H activation:: ruthenium-catalysed regioselective hydroamination of alkynes and hydroarylation of an alkene with N-methylaniline [J].
Uchimaru, Y .
CHEMICAL COMMUNICATIONS, 1999, (12) :1133-1134
[60]   Iron-Catalyzed Directed C2-Alkylation and Alkenylation of Indole with Vinylarenes and Alkynes [J].
Wong, Mun Yee ;
Yamakawa, Takeshi ;
Yoshikai, Naohiko .
ORGANIC LETTERS, 2015, 17 (03) :442-445